It is proposed to synthesize examples of those compounds possessing functional group distribution characteristic of the polyketide fungal metabolites. Three specific types of closely related compounds are considered 1) dihydro-gamma-pyrones and 3-furanones 2) 4-methoxy-5, 6- dihydro-alpha-pryones and 4-methoxy-2-furanones (beta-methoxy-delta- alpha, beta-butenolides) 3) 5,6-dihydro-alpha-pyrones and 2-furanones (delta alpha, beta-butenolides). The synthesis of representative antibiotics of these structural types will be facilitated by the development of several new synthetic methods intended for the general introduction of oxygenation patterns in a 1,3,4 or 1,3,5 relationship. Specific total syntheses are developed for such representative examples as Pestalotin, the Kawa lactones, Penicillic acid, and Massiolactone.